Homes under $500K in Monticello, FL
28 for sale · 65 homes listed · Updated November 9, 2026 · Page 1 of 2
- 640 Nautilus Drive, Monticello 32344 $459,000 · 2 bd · 1 ba · 1,200 sqft
- 220 Eaton Street, Monticello 32344 $239,000 · 3 bd · 1 ba · 1,164 sqft
- 398 Tecumseh Road, Monticello 32344 $499,000 · 5 bd · 2 ba · 2,268 sqft
- 8156 Waukeenah Highway, Monticello 32344 $349,000 · 3 bd · 2 ba · 1,774 sqft
- 110 Crooked Creek Lane, Monticello 32344 $459,900 · 3 bd · 2 ba · 1,883 sqft
- 1628 North Jefferson Highway, Monticello 32344 $398,900 · 3 bd · 3 ba · 3,127 sqft
- 670 Poplar Street, Monticello 32344 $149,900 · 3 bd · 1 ba · 1,312 sqft
- 1070 Partridge Lane, Monticello 32344 $298,900 · 3 bd · 2 ba · 1,351 sqft
- 1550 Tennessee Street, Monticello 32344 $200,000 · 3 bd · 2 ba · 1,304 sqft
- 947 Piney Woods Road, Monticello 32344 $325,000 · 4 bd · 2 ba · 2,304 sqft
- 78 Fen Court, Monticello 32344 $470,000 · 3 bd · 2 ba · 1,806 sqft
- 112 Long Leaf Drive, Monticello 32344 $250,000 · 3 bd · 2 ba · 1,980 sqft
- 515 Sunset Drive, Monticello 32344 $299,900 · 3 bd · 2 ba · 2,583 sqft
- 1605 Sweetbay Court, Monticello 32344 $360,500 · 3 bd · 2 ba · 1,464 sqft
- 1420 Tennessee Avenue, Monticello 32344 $116,500 · 3 bd · 2 ba · 1,716 sqft
- 535 Holly Road, Monticello 32344 $357,000 · 3 bd · 2 ba · 1,326 sqft
- 360 Bowman Street, Monticello 32344 $252,500 · 3 bd · 2 ba · 1,235 sqft
- 380 Poplar Street, Monticello 32344 $175,000 · 3 bd · 1 ba · 1,300 sqft
- 620 South Jefferson Street, Monticello 32344 $179,000 · 1 bd · 1 ba · 806 sqft
- 1410 East Pearl Street, Monticello 32344 $385,000 · 4 bd · 2 ba · 2,750 sqft
- 1195 East Pearl Street, Monticello 32344 $274,500 · 2 bd · 1 ba · 1,090 sqft
- 185 West Walnut Street, Monticello 32344 $279,000 · 3 bd · 3 ba · 1,880 sqft
- 68 East Hummingbird Lane, Monticello 32344 $425,000 · 3 bd · 3 ba · 2,898 sqft
- 1015 South Jefferson Street, Monticello 32344 $349,900 · 4 bd · 2 ba · 1,844 sqft
- 153 Ravencroft Road, Monticello 32344 $419,900 · 3 bd · 2 ba · 1,780 sqft
- 231 Osceola Lane, Monticello 32344 $209,000 · 2 bd · 2 ba · 993 sqft
- 855 South Waukeenah Street, Monticello 32344 $399,900 · 4 bd · 3 ba · 1,798 sqft
- 148 South Main Avenue, Monticello 32344 $225,000 · 3 bd · 2 ba · 1,568 sqft
- 34 West Hummingbird Lane, Monticello 32344 Active Under Contract $164,900 · 4 bd · 3 ba · 2,553 sqft
- 1511 Spring Hollow Road, Monticello 32344 Active Under Contract $259,000 · 3 bd · 2 ba · 1,338 sqft
- 1012 South Main Avenue, Monticello 32344 Active Under Contract $379,000 · 3 bd · 2 ba · 2,280 sqft
- 254 Woodland Drive, Monticello 32344 Active Under Contract $450,000 · 3 bd · 2 ba · 2,239 sqft
- 120 Larry South Lane, Monticello 32344 Active Under Contract $227,900 · 3 bd · 2 ba · 1,323 sqft
- 870 Shady Lane, Monticello 32344 Active Under Contract $150,000 · 3 bd · 1 ba · 1,366 sqft
- 339 Silver Lake Road, Monticello 32344 Active Under Contract $375,000 · 3 bd · 3 ba · 2,706 sqft
- 51 Tarn Way, Monticello 32344 Active Under Contract $469,997 · 3 bd · 2 ba · 1,890 sqft
- 340 South Waukeenah Street, Monticello 32344 Active Under Contract $90,000 · 3 bd · 1 ba · 1,864 sqft
- 285 Mallard Lane, Monticello 32344 Active Under Contract $429,000 · 3 bd · 2 ba · 2,000 sqft
- 1680 Willow Road, Monticello 32344 Active Under Contract $435,000 · 3 bd · 2 ba · 1,919 sqft
- 520 East High Street, Monticello 32344 Active Under Contract $175,000 · 3 bd · 2 ba · 1,825 sqft
- 2664 A West Washington Highway, Monticello 32344 Active Under Contract $325,000 · 5 bd · 2 ba · 2,659 sqft
- 73 West Bryant Court, Monticello 32344 Active Under Contract $295,000 · 4 bd · 2 ba · 1,760 sqft
- 12180 Gamble Road, Monticello 32344 Active Under Contract $299,900 · 3 bd · 2 ba · 1,575 sqft
- 196 Private Road, Monticello 32344 Active Under Contract $254,999 · 3 bd · 2 ba · 1,664 sqft
- 60 Bob White Trail, Monticello 32344 Active Under Contract $269,900 · 3 bd · 2 ba · 1,620 sqft
- 1565 Sweetbay Court, Monticello 32344 Active Under Contract $350,500 · 3 bd · 2 ba · 1,464 sqft
- 395 Sunset Drive, Monticello 32344 Active Under Contract $305,000 · 3 bd · 2 ba · 1,596 sqft
- 4081 Gamble Road, Monticello 32344 Active Under Contract $337,000 · 4 bd · 2 ba · 2,162 sqft
- 810 East Dogwood Street, Monticello 32344 Active Under Contract $235,000 · 3 bd · 1 ba · 1,700 sqft
- 304 Limestone Road, Monticello 32344 Active Under Contract $185,000 · 3 bd · 2 ba · 1,680 sqft